This thesis begins an exploration by creating an experiment that aims to demonstrate that the connection between mathematics, systems and typography can actually promote, rather than hinder, creative experimentation. Rather than constraining the designer, these structures and strict rules serve as a solid foundation upon which creativity and experimentation can flourish. By designing four different typefaces, it is sought to demonstrate that careful systematic approaches and grid-based frameworks can act as a catalyst for innovation and unleashing the designer’s creativity. The second objective of this experiment is posed as, to deepen the form of each letter as an image, where it will highlight the harmonious coexistence between algorithmic - mathematical rules and design freedom. Each font was designed based on a different creative concept and has three different weights. At the same time four different specimens were designed, where they present the alphabets in detail. All fonts are display fonts and contain uppercase Latin characters A-Z, numbers 0-9, and the glyphs !#()?-. In total each font has 44 glyphs and the family has 132 glyphs.